Green chemistry metrics and life-cycle analysis (LCA) were used to assess inefficiencies in two current organic chemistry experiments conducted in third-year organic chemistry to synthesize ("E")-stilbene from benzaldehyde. An alternative Wittig-based, greener, one-pot experiment using the same starting material was selected as a vehicle to introduce the concepts of green chemistry to students. The original learning objectives for the experiment were maintained with additional learning objectives in green chemistry introduced. The theoretical and experimental calculations of all experiments were compared using the standard univariate and multivariate metrics for LCA analysis, to assess the impact of chemical waste generated on the environment. The LCA metrics showed that the Wittig-based experiment addressed eight principles of green chemistry and possessed fewer environmental hazards, produced less waste (E-factor), and had better isomeric purity, mass, and process efficiency including factors such as global warming potential than the current lab methods. Results from a survey of students who conducted all three experiments indicated an enhanced knowledge of green chemistry and an improved sense of chemical and environmental impact. The research provided a platform to introduce sustainable chemistry practices to organic chemistry students at the undergraduate level.